Airbnb Properties for Sale in Chestertown, MD

Looking for a vacation rental investment in Chestertown, MD with high ROI ?

Explore a range of newly added short-term rental homes in Chestertown, MD. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Chestertown, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
0 Round Top Rd CHESTERTOWN, MD 0 Round Top Rd, CHESTERTOWN, MD 21620 \| Other	N/A beds \| N/A baths \| N/A	$200,000	Airbnb cash on cash: 3.57% Traditional cash on cash: 0.82% Airbnb Rental Income: $1625 Traditional Rental Income: $643 Airbnb ROI: 3.57% Traditional ROI: 0.82%
Airbnb Properties for Sale in Other Cities of Maryland
920 Cloverfields Dr STEVENSVILLE , MD Great location in a waterfront community! This 3 bedroom 1 bath is walking distance to poo...	3 beds \| 1 baths \| 1,248 sq.ft.	$405,000	Airbnb cash on cash: 2.55% Traditional cash on cash: 2.43% Airbnb Rental Income: $2210 Traditional Rental Income: $1609 Airbnb ROI: 2.55% Traditional ROI: 2.43%
10 Owen Ct PERRYVILLE , MD Great price on a beautiful renovated end unit townhouse. Hard wood floors, New Heat & Air,...	3 beds \| 1 baths \| 1,100 sq.ft.	$256,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 3.31% Airbnb Rental Income: $2094 Traditional Rental Income: $1323 Airbnb ROI: 4.28% Traditional ROI: 3.31%
27329 Iron Gate Rd FEDERALSBURG , MD Great opportunity to own this charming colonial style farm house with endless opportunity ...	3 beds \| 2 baths \| 2,038 sq.ft.	$475,000	Airbnb cash on cash: 4.19% Traditional cash on cash: 2.76% Airbnb Rental Income: $3424 Traditional Rental Income: $2027 Airbnb ROI: 4.19% Traditional ROI: 2.76%
2348 BOTELER ROAD BROWNSVILLE , MD Welcome to Your Dream Farmhouse Retreat! Located on a serene, fenced-in acre, this charmi...	3 beds \| 2 baths \| 1,504 sq.ft.	$312,000	Airbnb cash on cash: 8.47% Traditional cash on cash: 6.59% Airbnb Rental Income: $3963 Traditional Rental Income: $2563 Airbnb ROI: 8.47% Traditional ROI: 6.59%
119 Watkins Rd GRASONVILLE , MD Completely remodeled from top to bottom! Roof and siding replaced in 2019! Brand new Luxur...	3 beds \| 1 baths \| 1,515 sq.ft.	$374,600	Airbnb cash on cash: 5.33% Traditional cash on cash: 3.25% Airbnb Rental Income: $3176 Traditional Rental Income: $1726 Airbnb ROI: 5.33% Traditional ROI: 3.25%
17111 MANNING Drive ACCOKEEK , MD Discover the potential in this 1-story detached home set on over 2 acres in desirable Prin...	4 beds \| 2 baths \| 1,820 sq.ft.	$359,900	Airbnb cash on cash: 5.59% Traditional cash on cash: 5.42% Airbnb Rental Income: $3527 Traditional Rental Income: $2693 Airbnb ROI: 5.59% Traditional ROI: 5.42%
7126 ARCADIA CIRCLE Newark , MD Back on the market due to buyers unexpected personal emergency. . Newer construction nes...	3 beds \| 2 baths \| 1,214 sq.ft.	$305,000	Airbnb cash on cash: 7.41% Traditional cash on cash: 6.25% Airbnb Rental Income: $3505 Traditional Rental Income: $2398 Airbnb ROI: 7.41% Traditional ROI: 6.25%
15 S Mauldin Ave NORTH EAST , MD Price reduced. 1935 rancher located in the waterfront town of North East. Walk to your fa...	7 beds \| 4 baths \| 4,714 sq.ft.	$650,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 0.7% Airbnb Rental Income: $2130 Traditional Rental Income: $1422 Airbnb ROI: 0.97% Traditional ROI: 0.7%
205 GRAVEL RUN Road GRASONVILLE , MD Charming threebedroom, onebath rancher located at 205 Gravel Run Road in Grasonville, set ...	3 beds \| 1 baths \| 856 sq.ft.	$300,000	Airbnb cash on cash: 6.7% Traditional cash on cash: 4.64% Airbnb Rental Income: $3176 Traditional Rental Income: $1876 Airbnb ROI: 6.7% Traditional ROI: 4.64%
413 Rogers Ave Glen Burnie , MD Welcome to 413 Rogers Ave in the heart of Glen Burnie! This spacious townhome offers 4 bed...	4 beds \| 2 baths \| 1,434 sq.ft.	$314,200	Airbnb cash on cash: 6.34% Traditional cash on cash: 5.05% Airbnb Rental Income: $3277 Traditional Rental Income: $2161 Airbnb ROI: 6.34% Traditional ROI: 5.05%
401 LINDEN AVE Frederick , MD First Open House - Sat 1-3! Single-level living meets modern style in this beautifully ren...	5 beds \| 3 baths \| N/A	$729,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 1.23% Airbnb Rental Income: $2783 Traditional Rental Income: $1822 Airbnb ROI: 1.69% Traditional ROI: 1.23%
15 Georgia Ave NW Glen Burnie , MD Cozy Cape Code style home in great commuter location with four (4) bedrooms and two (2) ba...	4 beds \| 1 baths \| 1,140 sq.ft.	$415,000	Airbnb cash on cash: 4.78% Traditional cash on cash: 4.04% Airbnb Rental Income: $3277 Traditional Rental Income: $2256 Airbnb ROI: 4.78% Traditional ROI: 4.04%
2439 TODDVILLE RD WINGATE , MD Welcome to your ultimate hunting retreat nestled in the heart of nature's splendor! This 6...	5 beds \| 1 baths \| N/A	$479,900	Airbnb cash on cash: 2.34% Traditional cash on cash: 1.94% Airbnb Rental Income: $2230 Traditional Rental Income: $1493 Airbnb ROI: 2.34% Traditional ROI: 1.94%
9518 QUAIL HOLLOW #702 SAINT MICHAELS , MD Set within the sought-after Martingham community of Quail Hollow, backing to the top rated...	3 beds \| 3 baths \| 1,800 sq.ft.	$480,000	Airbnb cash on cash: 3.41% Traditional cash on cash: 3.41% Airbnb Rental Income: $3501 Traditional Rental Income: $2728 Airbnb ROI: 3.41% Traditional ROI: 3.41%
7704 HIGHPOINT ROAD CLEARWATER BEACH , MD Beautifully finished brand new construction....open floor concept, stainless steel applian...	3 beds \| 3 baths \| N/A	$489,900	Airbnb cash on cash: 8.16% Traditional cash on cash: 3.7% Airbnb Rental Income: $5820 Traditional Rental Income: $2617 Airbnb ROI: 8.16% Traditional ROI: 3.7%

Vacation Rentals in Chestertown

There are 1 vacation rental properties available for sale in the city of Chestertown . The median list price of Airbnb properties available for sale in Chestertown is $384,000 and the average price per square foot is $170. The cash on cash return on vacation rentals in Chestertown is 1.00%. The average monthly short term rental income in Chestertown is $1,988.

Chestertown, MD Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 1 Airbnb properties available for sale in Chestertown.

In 2026, the best neighborhood to buy short term rental property is CHESTERTOWN.

In May 2026, the average Airbnb occupancy rate in Chestertown is 24%.

Airbnb data on vacation rentals in Chestertown, MD is available at Mashvisor. You can access data such as listings, real-time pricing trends, Chestertown, MD market insights, guest information and booking details, seasonality trends and historical Chestertown, MD Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Chestertown, MD

0 Round Top Rd

CHESTERTOWN, MD

N/A beds | N/A baths | N/A

$200,000

Airbnb cash on cash: 3.57%

Traditional cash on cash: 0.82%

Airbnb Rental Income: $1625

Traditional Rental Income: $643

Airbnb ROI: 3.57%

Traditional ROI: 0.82%

Airbnb Properties for Sale in Other Cities of Maryland

STEVENSVILLE , MD

3 beds | 1 baths | 1,248 sq.ft.

$405,000

Airbnb cash on cash: 2.55%

Traditional cash on cash: 2.43%

Airbnb Rental Income: $2210

Traditional Rental Income: $1609

Airbnb ROI: 2.55%

Traditional ROI: 2.43%

PERRYVILLE , MD

3 beds | 1 baths | 1,100 sq.ft.

$256,000

Airbnb cash on cash: 4.28%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $2094

Traditional Rental Income: $1323

Airbnb ROI: 4.28%

Traditional ROI: 3.31%

FEDERALSBURG , MD

3 beds | 2 baths | 2,038 sq.ft.

$475,000

Airbnb cash on cash: 4.19%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $3424

Traditional Rental Income: $2027

Airbnb ROI: 4.19%

Traditional ROI: 2.76%

BROWNSVILLE , MD

3 beds | 2 baths | 1,504 sq.ft.

$312,000

Airbnb cash on cash: 8.47%

Traditional cash on cash: 6.59%

Airbnb Rental Income: $3963

Traditional Rental Income: $2563

Airbnb ROI: 8.47%

Traditional ROI: 6.59%

GRASONVILLE , MD

3 beds | 1 baths | 1,515 sq.ft.

$374,600

Airbnb cash on cash: 5.33%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $3176

Traditional Rental Income: $1726

Airbnb ROI: 5.33%

Traditional ROI: 3.25%

ACCOKEEK , MD

4 beds | 2 baths | 1,820 sq.ft.

$359,900

Airbnb cash on cash: 5.59%

Traditional cash on cash: 5.42%

Airbnb Rental Income: $3527

Traditional Rental Income: $2693

Airbnb ROI: 5.59%

Traditional ROI: 5.42%

Newark , MD

3 beds | 2 baths | 1,214 sq.ft.

$305,000

Airbnb cash on cash: 7.41%

Traditional cash on cash: 6.25%

Airbnb Rental Income: $3505

Traditional Rental Income: $2398

Airbnb ROI: 7.41%

Traditional ROI: 6.25%

NORTH EAST , MD

7 beds | 4 baths | 4,714 sq.ft.

$650,000

Airbnb cash on cash: 0.97%

Traditional cash on cash: 0.7%